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Southold, NY 55+ active adult communities & homes for sale - Page 3

94 communities near Southold

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Clockmaker's Hill
$100Ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
Bidwell Village
$300Ks - $400Ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
Billingsgate
$400Ks - $600Ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Boulder Brook
$200Ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Oak Meadow Estates
$400Ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
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Questions? Call us: (631) 407-2675
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes
Autumn Estates
$500Ks - $600Ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
Bartlett Hollow
$200Ks - $400Ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
RiverBend Estates
$400Ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Granite Woods
$600Ks - $700Ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Pines at Bohemia
$400Ks - $500Ks
The Pines at Bohemia, Bohemia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 20 homes
Summer Wind Estates
$300Ks - $400Ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 homes
Newington Ridge Preserve
$300Ks - $400Ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Cobblestone Court
$400Ks - $500Ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes
Want to learn more about 55+ rental communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Stone Ridge Estates 108 JOSEPH LN, DIX HILLS, NY, 11746, Dix Hills, NY 11746
$799,999

2 beds

|

2 baths

|

1,695 sq ft

|

Condo

108 JOSEPH LN, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
New Fairfield at St. James 101 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$449,000

1 beds

|

2 baths

|

900 sq ft

|

Condo

101 FLAIR CT, SMITHTOWN, NY, 11780
The Vineyards at Miller Place 45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764
$650,000

2 beds

|

3 baths

|

1,853 sq ft

|

Condo

45 HALLEY LN, MILLER PLACE, NY, 11764
New Meadowbrook Pointe Links & Spa 146 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763
$749,990

2 beds

|

3 baths

|

2,047 sq ft

|

Condo

146 AUGUSTA DR, MEDFORD, NY, 11763
Leisure Village 171B VENTRY CT 171B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$249,000

1 beds

|

1 baths

|

679 sq ft

|

Condo

171B VENTRY CT 171B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Want to learn more about 55+ rental communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
New Westhampton Pines 39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11..., Westhampton, NY 11977
$1,495,000

3 beds

|

2 baths

|

2,500 sq ft

|

Condo

39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11...
Community: Westhampton Pines
The Manors at The Colony Preserve 41 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967
$535,000

2 beds

|

2 baths

|

1,800 sq ft

|

Condo

41 GREENTREE CT, SHIRLEY, NY, 11967
Leisure Village 278 BERWICK CT UNIT B B, RIDGE, NY, 1196..., Ridge, NY 11961
$369,900

2 beds

|

1 baths

|

875 sq ft

|

Condo

278 BERWICK CT UNIT B B, RIDGE, NY, 1196...
Community: Leisure Village
Greenwood Village 42 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$99,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

42 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Greenwood Village 82 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$189,900

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

82 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Greenwood Village 164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$149,997

2 beds

|

2 baths

|

938 sq ft

|

Condo

164 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Greenwood Village 19 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949
$149,900

2 beds

|

2 baths

|

871 sq ft

|

Condo

19 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
Leisure Village 418 WEYMOUTH CT B, RIDGE, NY, 11961, Ridge, NY 11961
$364,999

2 beds

|

1 baths

|

1,036 sq ft

|

Condo

418 WEYMOUTH CT B, RIDGE, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Foxwood Village 1407 MIDDLE RD 275, CALVERTON, NY, 11933, Calverton, NY 11933
$425,000

3 beds

|

2 baths

|

1,530 sq ft

|

House

1407 MIDDLE RD 275, CALVERTON, NY, 11933
Community: Foxwood Village
Plymouth Estates at Mount Sinai 166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$579,999

2 beds

|

2 baths

|

1,820 sq ft

|

House

166 IRA RD, MOUNT SINAI, NY, 11766
Want to learn more about 55+ rental communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
New Fairfield at St. James 1107 CABOT CT N, SAINT JAMES, NY, 11780, Saint James, NY 11780
$439,990

1 beds

|

2 baths

|

929 sq ft

|

Condo

1107 CABOT CT N, SAINT JAMES, NY, 11780
New Greenwood Village 54 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949
$130,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

54 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Leisure Village 405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961
$290,000

2 beds

|

1 baths

|

874 sq ft

|

Condo

405 WOODBRIDGE DR D, RIDGE, NY, 11961
Community: Leisure Village
Country Village Estates 163 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727
$455,000

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

163 THEODORE DR, CORAM, NY, 11727
Leisure Village 423 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961
$247,500

1 beds

|

1 baths

|

782 sq ft

|

Condo

423 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Leisure Glen 10 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961
$599,900

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

10 OAKDALE CT, RIDGE, NY, 11961
Community: Leisure Glen
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Stone Ridge Estates 153 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746
$775,000

2 beds

|

2 baths

|

1,415 sq ft

|

Condo

153 CHRISTINE DR, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
Greenwood Village 91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$155,000

2 beds

|

2 baths

|

938 sq ft

|

Condo

91 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
The Waterways at Moriches 554 MIRROR POND CT, MORICHES, NY, 11955, Moriches, NY 11955
$525,000

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

554 MIRROR POND CT, MORICHES, NY, 11955
Stoneleigh Woods at Riverhead 23 GOOSE NECK LN, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$585,000

2 beds

|

3 baths

|

1,631 sq ft

|

Condo

23 GOOSE NECK LN, RIVERHEAD, NY, 11901
Want to learn more about 55+ rental communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Leisure Village 169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961
$289,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

169 VENTRY CT A, RIDGE, NY, 11961
Community: Leisure Village
Fairfield at St. James 504 GOTHAM CT, SAINT JAMES, NY, 11780, Saint James, NY 11780
$499,995

1 beds

|

2 baths

|

1,036 sq ft

|

House

504 GOTHAM CT, SAINT JAMES, NY, 11780
Fairfield at St. James 901 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780
$499,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

901 FENWAY RD, SAINT JAMES, NY, 11780
Leisure Village 128 EXMORE CT UNIT D, RIDGE, NY, 11961, Ridge, NY 11961
$319,900

2 beds

|

1 baths

|

1,278 sq ft

|

Condo

128 EXMORE CT UNIT D, RIDGE, NY, 11961
Community: Leisure Village
Encore Atlantic Shores 6 OVATION PL, EASTPORT, NY, 11941, Eastport, NY 11941
$795,000

2 beds

|

2 baths

|

2,150 sq ft

|

Condo

6 OVATION PL, EASTPORT, NY, 11941
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Leisure Village 116 EXMORE CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

116 EXMORE CT UNIT B, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 164 FALMOUTH CT E, RIDGE, NY, 11961, Ridge, NY 11961
$279,000

2 beds

|

1 baths

|

819 sq ft

|

Condo

164 FALMOUTH CT E, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 186 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961
$289,000

2 beds

|

1 baths

|

900 sq ft

|

Condo

186 VENTRY CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
The Waterways at Moriches 414 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955
$535,000

2 beds

|

2 baths

|

2,141 sq ft

|

Condo

414 LINDSAY LN, MORICHES, NY, 11955
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Stoneleigh Woods at Riverhead 5 NEWCASTLE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$635,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

5 NEWCASTLE CT, RIVERHEAD, NY, 11901
Want to learn more about 55+ rental communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
Leisure Knoll 190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961
$434,999

2 beds

|

1 baths

|

787 sq ft

|

Condo

190 CANTERBURY DR, RIDGE, NY, 11961
Community: Leisure Knoll
Leisure Village 373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961
$415,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
Fairfield at St. James 401 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$485,000

1 beds

|

2 baths

|

900 sq ft

|

Condo

401 CABOT CT, SMITHTOWN, NY, 11780
Want to learn more about 55+ communities in Southold? 55places can help!
Questions? Call us: (631) 407-2675
The Villages at Mount Sinai Park 4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$775,000

3 beds

|

3 baths

|

2,850 sq ft

|

House

4 OAKHURST CT, MOUNT SINAI, NY, 11766
Greenwood Village 77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$149,500

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

77 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village

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